Drs. Muspratt and Hofmann on Toluidine. 183 



were submitted to distillation in glass retorts, partly over an 

 open fire and partly on a sand-bath. There passes over at 

 first aqueous vapour, and when the temperature is sufficiently 

 elevated, a large quantity of benzoic acid (with a slight admix- 

 ture of cinnamic acid), which solidifies immediately in the 

 recipient into a white crystalline mass. As soon as the fluid 

 distilling over no longer solidified the receiver was changed, 

 and then there condensed a yellow liquid*, which is, accord- 

 ing to Deville, a mixture o^ toluole and benzoic cether. When 

 it had cooled — a quantity of benzoic acid previously dissolved 

 was deposited — we redistilled and only collected the portions 

 passing over from 130° — 140° C. This distillate is deprived 

 of the last traces of benzoic acid by being repeatedly distilled 

 with pieces of solid potash. The fluid obtained in this way 

 possessed nearly all the properties ascribed by Deville to 

 toluole. The product, however, in this manner is extremely 

 small when compared with the quantity of Tolu balsam em- 

 ployed. We have, on account of this, endeavoured to dis- 

 cover another source for getting the toluole in larger quan- 

 tities, but without success ; we therefore deem it necessary to 

 mention this, as it may spare perhaps other vain attempts. 



Cahoursf has occasionally found in his investigation upon 

 gaultheria oil that the salicylate of the oxide of methyle, when 

 distilled with caustic barytes, furnishes anisole, the same pro- 

 duct that the anisic acid isomeric with the former yields under 

 the same circumstances. 



Ci6 Hg Og + 2BaO = C,4 Hg O^ + 2(BaO, COg). 



* . ' I , . 



Salicylate of the Anisole. 



oxide of methyle. Dracole. 



This unexpected transformation seemed to point out a new 

 source for the production of manifold hydrurets of carbon, by 

 treating in a similar manner the various compound aethers. 



Anisole differs only from toluole in two equivalents of 

 oxygen. 



Anisole Cj4 Hg Og 

 Toluole Cj4 Hg 



The question now presented itself as to whether toluole could 

 not be produced by the action of caustic barytes or caustic 

 lime upon an aether containing two equivalents less of oxygen 

 than the salicylate of the oxide of methyle ? Such an aether 

 is the benzoale of the oxide of methyle : — 



* The crystalline mass collected in the first receiver contains likewise 

 a large quantity of the same liquid, which can be separated by mere distilla- 

 tion with water. 



I Jnn. de Chim, et dc Pliys. 3 ser. vol. x. p. 353. 



